Danofloxacin

Danofloxacin	Last updated: 14/09/2025
(Not known by any other names)

GENERAL INFORMATION

Description

A synthetic fluoroquinolone broad spectrum antibacterial and antimicrobial veterinary treatment active against both gram-positive and gram-negative bacteria

Examples of veterinary uses

Used to control nfections of the respiratory tract and intestinal tract including bovine respiratory disease associated with Mannheimia (Pasteurella) haemolytica and Pasteurella multocida

Examples of species treated

Cattle; Pigs; Domestic fowl

Approval status

VMR 2013/2033 approval status (GB/UK)

Approved - usually supplied as a prescription only medicine to be authorised by a veterinarian (POM-V)

EU Regulatory approval status

Approved

Chemical structure

Isomerism

Danofloxacin exhibits stereoisomerism, specifically chirality, due to the presence of multiple chiral centres in its molecular structure. These chiral centres are located within the diazabicyclo[2.2.1]heptane ring system and the cyclopropyl group attached to the quinolone core. This configuration gives rise to distinct enantiomers. The biologically active form used in veterinary medicine is the (1S)-enantiomer. Additionally, danofloxacin can exist in different ionic forms, such as zwitterionic and neutral molecules, depending on its crystalline state. The zwitterionic form, observed in danofloxacin dihydrate, features both positive and negative charges within the same molecule, stabilised by hydrogen bonding and stacking interactions in the crystal lattice.

Chemical formula

C₁₉H₂₀FN₃O₃

Canonical SMILES

CN1CC2CC1CN2C3=C(C=C4C(=C3)N(C=C(C4=O)C(=O)O)C5CC5)F

Isomeric SMILES

CN1C[C@@H]2C[C@H]1CN2C3=C(C=C4C(=C3)N(C=C(C4=O)C(=O)O)C5CC5)F

International Chemical Identifier key (InChIKey)

QMLVECGLEOSESV-RYUDHWBXSA-N

International Chemical Identifier (InChI)

InChI=1S/C19H20FN3O3/c1-21-7-12-4-11(21)8-22(12)17-6-16-13(5-15(17)20)18(24)14(19(25)26)9-23(16)10-2-3-10/h5-6,9-12H,2-4,7-8H2,1H3,(H,25,26)/t11-,12-/m0/s1

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
danofloxacin dihydrate	Hydrate

General status

Veterinary substance type

Antibacterial, Antimicrobial

Substance groups

Fluoroquinolone drug

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Inhibits DNA gyrase and triggers induction of the SOS response and temperate bacteriophages

Molecular targets

[DNA gyrase subunit A, Antagonist]

CAS RN

112398-08-0

EC number

638-772-1

CIPAC number

US EPA chemical code

PubChem CID

71335

Therapeutic Class

Antiinfectants for systemic use: Antibacterials for systemic use

ATCvet Code

QJ01MA92

Controlled Drug?

Regulation 37/2010 MRL Classification

Allowed substance (Table 1: All food producing species)

Molecular mass

357.37

PIN (Preferred Identification Name)

IUPAC name

1-cyclopropyl-6-fluoro-7-[(1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl]-4-oxoquinoline-3-carboxylic acid

CAS name

Forever chemical

Other status information

Relevant Environmental Water Quality Standards

Physical state

Related substances & organisms

danofloxacin mesylate

Commercial

Property

Value

Availability status

Current

Introduction & key dates

Circa 2000, introduced

Example manufacturers & suppliers of products using this active now or historically

Pzifer Animal Health

Example products using this active

Advocina

Formulation and application details

Usually supplied as a solution for injection

Commercial production

Danofloxacin is synthesised through a multi-step chemical process that begins with the preparation of a key intermediate: (1S,4S)-2,5-diazabicyclo[2.2.1]heptane. This compound is reacted with cyclopropanecarboxylic acid under controlled heating to form the core quinolone structure via a condensation reaction. The resulting danofloxacin base is then treated with methanesulfonic acid in water to form danofloxacin mesylate, a more stable and bioavailable salt form. The solution is refluxed to complete salification, followed by gradual cooling to crystallise the product.

Impact on climate of production and use

Published GHG data is not available for most pharmaceuticals. However, according to industry, global averages suggest producing 1 kg of a typical active pharmaceutical ingredient can range from 10 to 100 kg CO₂e for small molecule drugs and potentially up to 1000 kg CO₂e for complex biologicals such as vaccines, depending on the drug type, its formulation, complexity of synthesis, solvent recovery, and energy sources used.

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

Solubility - In water at 20 °C (mg l⁻¹)

Solubility - In organic solvents at 20 °C (mg l⁻¹)

Melting point (°C)

263

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

Octanol-water partition coefficient at pH 7, 20 °C

Log P

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

Henry's law constant at 25 °C (Pa m³ mol⁻¹)

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

Maximum UV-vis absorption L mol⁻¹ cm⁻¹

Surface tension (mN m⁻¹)

Refractive Index

Environmental release

Released intermittently into the environment via faeces and urine of medicated animals as well as via the spreading of manure

Degradation

Property

Value

Source; quality score; and other information

Interpretation

Soil degradation (days) (aerobic)

DT₅₀ (typical)

115

Persistent

DT₅₀ (lab at 20 °C)

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

Note

US EPA data gives DT₅₀ range 91-143 days, Soils=3

Manure DT₅₀ (days)

Aqueous photolysis DT₅₀ (days) at pH 7

Value

0.003

Fast

Note

Very rapid: 4.3 minutes at pH 7

Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7

Value

Stable

Note

Stable at pH 5-9

Water-sediment DT₅₀ (days)

Water phase only DT₅₀ (days)

Sediment phase only DT₅₀ (days)

Air degradation

As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below.

Decay in stored produce DT₅₀

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

2837

as mesylate variant

Non-mobile

K_oc (mL g⁻¹)

284533

Notes and range

K_d range 2280-3800 mL g⁻¹, K_foc range 75699-644000 mL g⁻¹, Soils=3; Data for faecal adsorption; K_d range 138-541 mL g⁻¹, K_oc range 323-1036 mL g⁻¹

Freundlich

K_f (mL g⁻¹)

K_foc (mL g⁻¹)

¹/_n

Notes and range

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-3.00

Calculated

Low leachability

Bio-concentration factor

BCF (l kg⁻¹)

CT₅₀ (days)

Known soil metabolites

Metabolite

Major/Minor fraction

$Click here for further information on Major/Minor fraction$

Estimated maximum occurrence fraction

Notes

N-desmethyldanofloxacin

USEPA data

7-aminodanofloxacin

USEPA data

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

N-desmethyldanofloxacin

Cattle

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)

Birds - Acute LD₅₀ (mg kg⁻¹)

Birds - Short term dietary (LC₅₀/LD₅₀)

Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹ dw soil)

> 1200

Lumbricus terrestris as mesylate

Low

Earthworms - Chronic NOEC, reproduction (mg kg⁻¹ dw soil)

Soil micro-organisms

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

Vegetative vigour ER₅₀ (g ha⁻¹)

Seedling emergence ER₅₀ (g ha⁻¹)

Honeybees (Apis spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Chronic

Notes

Bumblebees (Bombus spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Mason bees (Osmia spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Other bee species (1)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Other bee species (2)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Beneficial insects (Ladybirds)

Beneficial insects (Lacewings)

Beneficial insects (Parasitic wasps)

Beneficial insects (Predatory mites)

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)

Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

Temperate Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

Temperate Freshwater Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)

Tropical Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)

Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)

Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)

Aquatic Plants (free-floating, fonds growth, fresh) - 7 day (mg l⁻¹)

Aquatic plants (rooted, growth rate, fresh) - 14 day (mg l⁻¹)

Algae - Acute (growth rate, fresh; mg l⁻¹)

Algae - Chronic (growth rate, fresh; mg l⁻¹)

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves

HUMAN HEALTH AND PROTECTION

General

Property

Value

Source; quality score; and other information

Interpretation

Threshold of Toxicological Concern (Cramer Class)

High (class III)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2000

Rat

Low

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 10.0

Rat

Other Mammal toxicity endpoints

Intravenous LD₅₀ = 75 mg l⁻¹

Mouse

ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)

ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)

AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

Exposure Routes

Public

Occupational

Mammalian dose elimination route and rate

In rats, dogs and pigs it is excreted in the unchanged form in the urine

Health issues

Specific human health issues (hazard-based)

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

May cause gastrointestinal problems

Handling issues

Property

Value and interpretation

General

No information available

CLP classification 2013

WHO Classification

Not listed (Not listed)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

danofloxacin

French

danofloxacine

German

Danish

Italian

danofloxacino

Spanish

danofloxacino

Greek

Polish

Swedish

Hungarian

Dutch

Norwegian

Record last updated:	14/09/2025
Contact:	aeru@herts.ac.uk
Please cite as:	Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242